2-(4-Chloro­anilino)-1-phenyl­ethanone

Yao, X.-J.; Yuan, Q.

doi:10.1107/S1600536811006404

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o710

doi:10.1107/S1600536811006404

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2-(4-Chloroanilino)-1-phenylethanone

Xing-Jun Yao ^a ^* and Qian Yuan ^b

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, 252059 Liaocheng, Shandong, People's Republic of China, and ^bGuodian Liaocheng Power Co. Ltd, 252033 Liaocheng, Shandong, People's Republic of China
^*Correspondence e-mail: y_xingjun01@163.com

(Received 16 February 2011; accepted 20 February 2011; online 26 February 2011)

In the title compound, C₁₄H₁₂ClNO, the planes of the two aromatic rings form a dihedral angle of 4.16 (1)°. The molecule is essentially planar with an r.m.s. deviation for all non-H atoms of 0.0372 Å.

Related literature

For a related structure, see: Anilkumar et al. (2005 ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Triclinic, $[P \overline 1]$
a = 5.6500 (5) Å
b = 7.3921 (8) Å
c = 13.9769 (14) Å
α = 98.588 (2)°
β = 91.095 (1)°
γ = 97.590 (1)°
V = 571.70 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.954, T_max = 0.969
2924 measured reflections
1971 independent reflections
1238 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.178
S = 1.03
1971 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006404/ng5121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006404/ng5121Isup2.hkl

checkCIF report

Comment top

The title compound, C₁₄H₁₂ClNO, is often used as catalyst for the polymerization of olefins and as a reactant in organic synthesis. The molecule of (I) is shown in Fig. 1. The bond lengths and angles are normal. The dihedral angle between the two benzene rings is 4.16 (1) °. The molecule is essentially planar, the r.m.s. deviation for all non-H atoms being 0.0372 Å.

Related literature top

For a related structure, see: Anilkumar et al. (2005).

Experimental top

The title compound was synthesized by the reaction of 4-chloroaniline (1 mmol, 127.6 mg) with 2-bromo-1-phenylethanone (1 mmol, 199.0 mg) in ethanol (20 ml) under reflux conditions (338 K) for 3 h. The solvent was removed and the solid product recrystallized from ethanol. After six days brown crystals were obtained that were suitable for X-ray diffraction study.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atomic labeling and 30% probability displacement ellipsoids.

2-(4-Chloroanilino)-1-phenylethanone top

Crystal data top

C₁₄H₁₂ClNO	Z = 2
M_r = 245.70	F(000) = 256
Triclinic, P1	D_x = 1.427 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6500 (5) Å	Cell parameters from 945 reflections
b = 7.3921 (8) Å	θ = 2.8–24.4°
c = 13.9769 (14) Å	µ = 0.31 mm⁻¹
α = 98.588 (2)°	T = 298 K
β = 91.095 (1)°	Block, brown
γ = 97.590 (1)°	0.15 × 0.12 × 0.10 mm
V = 571.70 (10) Å³

Data collection top

Bruker SMART APEX diffractometer	1971 independent reflections
Radiation source: fine-focus sealed tube	1238 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
T_min = 0.954, T_max = 0.969	k = −7→8
2924 measured reflections	l = −13→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1P)² + 0.0005P] where P = (F_o² + 2F_c²)/3
1971 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO	γ = 97.590 (1)°
M_r = 245.70	V = 571.70 (10) Å³
Triclinic, P1	Z = 2
a = 5.6500 (5) Å	Mo Kα radiation
b = 7.3921 (8) Å	µ = 0.31 mm⁻¹
c = 13.9769 (14) Å	T = 298 K
α = 98.588 (2)°	0.15 × 0.12 × 0.10 mm
β = 91.095 (1)°

Data collection top

Bruker SMART APEX diffractometer	1971 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1238 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.969	R_int = 0.032
2924 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
1971 reflections	Δρ_min = −0.36 e Å⁻³
154 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.43122 (17)	0.65041 (13)	0.83483 (7)	0.0650 (4)
N1	0.1395 (5)	0.7998 (4)	0.5053 (2)	0.0506 (8)
H1	0.2852	0.8498	0.5179	0.061*
O1	0.4464 (4)	0.8715 (3)	0.37523 (18)	0.0598 (7)
C1	0.0566 (6)	0.7594 (4)	0.4079 (2)	0.0413 (8)
H1A	−0.0764	0.8266	0.3988	0.050*
H1B	−0.0005	0.6285	0.3920	0.050*
C2	0.2487 (6)	0.8107 (4)	0.3420 (2)	0.0415 (8)
C3	0.1916 (5)	0.7858 (4)	0.2383 (2)	0.0405 (8)
C4	−0.0282 (6)	0.7083 (4)	0.1998 (2)	0.0533 (9)
H4	−0.1467	0.6676	0.2399	0.064*
C5	−0.0752 (7)	0.6900 (5)	0.1028 (3)	0.0706 (12)
H5	−0.2255	0.6365	0.0769	0.085*
C6	0.0965 (8)	0.7495 (5)	0.0435 (3)	0.0737 (12)
H6	0.0634	0.7377	−0.0228	0.088*
C7	0.3167 (8)	0.8265 (5)	0.0813 (3)	0.0700 (12)
H7	0.4348	0.8671	0.0410	0.084*
C8	0.3635 (6)	0.8438 (4)	0.1780 (2)	0.0536 (10)
H8	0.5146	0.8959	0.2036	0.064*
C9	0.0012 (5)	0.7637 (4)	0.5807 (2)	0.0363 (7)
C10	0.0950 (6)	0.8121 (4)	0.6740 (2)	0.0424 (8)
H10	0.2520	0.8695	0.6842	0.051*
C11	−0.0353 (6)	0.7783 (4)	0.7514 (2)	0.0446 (8)
H11	0.0313	0.8129	0.8139	0.054*
C12	−0.2643 (6)	0.6932 (4)	0.7368 (2)	0.0412 (8)
C13	−0.3618 (6)	0.6439 (4)	0.6462 (3)	0.0449 (8)
H13	−0.5185	0.5854	0.6369	0.054*
C14	−0.2313 (6)	0.6795 (4)	0.5679 (2)	0.0445 (8)
H14	−0.3004	0.6466	0.5057	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0711 (7)	0.0651 (7)	0.0599 (7)	0.0021 (5)	0.0184 (5)	0.0176 (5)
N1	0.0441 (17)	0.0607 (19)	0.0426 (18)	−0.0048 (14)	0.0015 (13)	0.0045 (14)
O1	0.0500 (16)	0.0705 (18)	0.0540 (16)	−0.0095 (13)	−0.0005 (13)	0.0097 (13)
C1	0.0433 (19)	0.0377 (19)	0.042 (2)	0.0048 (15)	0.0009 (16)	0.0047 (15)
C2	0.044 (2)	0.0269 (17)	0.053 (2)	0.0003 (15)	0.0030 (17)	0.0074 (14)
C3	0.050 (2)	0.0285 (17)	0.043 (2)	0.0070 (15)	0.0045 (16)	0.0044 (14)
C4	0.054 (2)	0.060 (2)	0.044 (2)	0.0007 (18)	0.0003 (18)	0.0076 (17)
C5	0.069 (3)	0.082 (3)	0.057 (3)	0.003 (2)	−0.011 (2)	0.006 (2)
C6	0.099 (4)	0.077 (3)	0.045 (2)	0.009 (3)	−0.001 (2)	0.015 (2)
C7	0.091 (3)	0.062 (3)	0.057 (3)	−0.003 (2)	0.020 (2)	0.018 (2)
C8	0.063 (2)	0.044 (2)	0.051 (2)	−0.0021 (17)	0.0072 (18)	0.0044 (16)
C9	0.0419 (18)	0.0278 (17)	0.0393 (19)	0.0074 (14)	0.0003 (15)	0.0032 (13)
C10	0.0364 (17)	0.0358 (19)	0.053 (2)	−0.0030 (14)	−0.0031 (16)	0.0059 (15)
C11	0.050 (2)	0.044 (2)	0.0389 (19)	0.0025 (16)	−0.0033 (16)	0.0058 (15)
C12	0.046 (2)	0.0348 (18)	0.045 (2)	0.0078 (15)	0.0086 (16)	0.0104 (14)
C13	0.0369 (18)	0.041 (2)	0.054 (2)	−0.0004 (15)	0.0013 (16)	0.0021 (16)
C14	0.043 (2)	0.048 (2)	0.0388 (19)	0.0025 (16)	−0.0054 (16)	−0.0010 (15)

Geometric parameters (Å, º) top

Cl1—C12	1.723 (3)	C6—C7	1.360 (5)
N1—C9	1.361 (4)	C6—H6	0.9300
N1—C1	1.407 (4)	C7—C8	1.356 (5)
N1—H1	0.8600	C7—H7	0.9300
O1—C2	1.204 (4)	C8—H8	0.9300
C1—C2	1.485 (4)	C9—C14	1.374 (4)
C1—H1A	0.9700	C9—C10	1.376 (5)
C1—H1B	0.9700	C10—C11	1.355 (4)
C2—C3	1.457 (4)	C10—H10	0.9300
C3—C4	1.362 (4)	C11—C12	1.359 (5)
C3—C8	1.367 (4)	C11—H11	0.9300
C4—C5	1.360 (4)	C12—C13	1.350 (5)
C4—H4	0.9300	C13—C14	1.370 (4)
C5—C6	1.359 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300

C9—N1—C1	123.4 (3)	C8—C7—C6	119.8 (3)
C9—N1—H1	118.3	C8—C7—H7	120.1
C1—N1—H1	118.3	C6—C7—H7	120.1
N1—C1—C2	111.2 (3)	C7—C8—C3	120.9 (3)
N1—C1—H1A	109.4	C7—C8—H8	119.6
C2—C1—H1A	109.4	C3—C8—H8	119.6
N1—C1—H1B	109.4	N1—C9—C14	122.6 (3)
C2—C1—H1B	109.4	N1—C9—C10	119.6 (3)
H1A—C1—H1B	108.0	C14—C9—C10	117.8 (3)
O1—C2—C3	121.9 (3)	C11—C10—C9	121.8 (3)
O1—C2—C1	119.4 (3)	C11—C10—H10	119.1
C3—C2—C1	118.7 (3)	C9—C10—H10	119.1
C4—C3—C8	119.0 (3)	C10—C11—C12	119.3 (3)
C4—C3—C2	122.2 (3)	C10—C11—H11	120.3
C8—C3—C2	118.9 (3)	C12—C11—H11	120.3
C5—C4—C3	120.3 (3)	C13—C12—C11	120.4 (3)
C5—C4—H4	119.9	C13—C12—Cl1	120.0 (3)
C3—C4—H4	119.9	C11—C12—Cl1	119.6 (3)
C6—C5—C4	120.3 (4)	C12—C13—C14	120.4 (3)
C6—C5—H5	119.9	C12—C13—H13	119.8
C4—C5—H5	119.9	C14—C13—H13	119.8
C5—C6—C7	119.9 (4)	C13—C14—C9	120.3 (3)
C5—C6—H6	120.1	C13—C14—H14	119.9
C7—C6—H6	120.1	C9—C14—H14	119.9

C9—N1—C1—C2	−178.9 (3)	C2—C3—C8—C7	−178.8 (3)
N1—C1—C2—O1	2.6 (4)	C1—N1—C9—C14	1.8 (5)
N1—C1—C2—C3	−177.4 (2)	C1—N1—C9—C10	−178.3 (3)
O1—C2—C3—C4	176.5 (3)	N1—C9—C10—C11	−179.7 (3)
C1—C2—C3—C4	−3.5 (4)	C14—C9—C10—C11	0.1 (5)
O1—C2—C3—C8	−4.2 (4)	C9—C10—C11—C12	0.5 (5)
C1—C2—C3—C8	175.8 (2)	C10—C11—C12—C13	−0.4 (5)
C8—C3—C4—C5	−0.3 (2)	C10—C11—C12—Cl1	−179.8 (2)
C2—C3—C4—C5	179.0 (3)	C11—C12—C13—C14	−0.2 (5)
C3—C4—C5—C6	−0.2 (2)	Cl1—C12—C13—C14	179.2 (2)
C4—C5—C6—C7	0.5 (4)	C12—C13—C14—C9	0.8 (5)
C5—C6—C7—C8	−0.2 (5)	N1—C9—C14—C13	179.0 (3)
C6—C7—C8—C3	−0.4 (5)	C10—C9—C14—C13	−0.8 (5)
C4—C3—C8—C7	0.6 (4)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.6500 (5), 7.3921 (8), 13.9769 (14)
α, β, γ (°)	98.588 (2), 91.095 (1), 97.590 (1)
V (Å³)	571.70 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.954, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	2924, 1971, 1238
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.178, 1.03
No. of reflections	1971
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

References

Anilkumar, H. G., Yathirajan, H. S., Nagaraja, P. & Bolte, M. (2005). Acta Cryst. E61, o2551–o2552. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar